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Regioselective,Solvent‐ and Metal‐Free Chalcogenation of Imidazo[1,2‐a]pyridines by Employing I2/DMSO as the Catalytic Oxidation System
Authors:Dr. Jamal Rafique  Dr. Sumbal Saba  Dr. Alisson R. Rosário  Prof. Dr. Antonio L. Braga
Affiliation:1. http://labselen.ufsc.com/ 0000-0002-2336-040X Departamento de Química, Universidade Federal de Santa Catarina, Florianopolis, Brazil;2. Departamento de Química, Universidade Federal de Santa Catarina, Florianopolis, Brazil
Abstract:
Highly efficient molecular‐iodine‐catalyzed chalcogenations (S and Se) of imidazo[1,2‐a]pyridines were achieved by using diorganoyl dichalcogenides under solvent‐free conditions. This approach afforded the desired products that had been chalcogenated regioselectively at the C3 position in up to 96 % yield by using DMSO as an oxidant, in the absence of a metal catalyst, and under an inert atmosphere. This mild, green approach allowed the preparation of different types of chalcogenated imidazo[1,2‐a]pyridines with structural diversity. Furthermore, the current protocol was also extended to other N‐heterocyclic cores.
Keywords:green chemistry  iodine  nitrogen heterocycles  selenium  sulfur
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